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Hexamethyldisilazane → 1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)ethanone

HRID 2246697
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HRID 2246697 반응식
[Na].C[Si](C)(C)N[Si](C)(C)C.[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[CH2:19][C:20]([OH:22])=O.[Cl:23][C:24]1[CH:33]=[CH:32][C:27](C(OC)=O)=[CH:26][CH:25]=1>C1COCC1>[Cl:23][C:24]1[CH:33]=[CH:32][C:27]([C:20](=[O:22])[CH2:19][C:13]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=2[Cl:11])=[CH:26][CH:25]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 13838HexamethyldisilazaneHCID 14307Methyl 4-chlorobenzoateHCID 882092,4-Dichlorophenylacetic acidHCID 5360545Sodium

생성물 1

HCID 5872691-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)ethanone수율 74.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매
3회

실험 절차

411 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF are cooled to −60° C., under a nitrogen atmosphere, 350 ml of THF are added, followed dropwise by a solution of 67.7 g of 2,4-dichlorophenylacetic acid in 70 ml of THF and the mixture is kept stirred for 2 hours while the temperature is maintained below −40° C. 53.5 g of methyl 4-chlorobenzoate are then added dropwise and at −60° C. and the mixture is kept stirred while the temperature is allowed to rise to 10° C. The reaction mixture is poured over an ice/1 liter 2N HCl mixture, the organic phase is washed with a saturated NaHCO3 solution, with water, extracted with ether, the organic phase is dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is taken up in pentane and the crystallized product formed is drained. 70 g of the expected compound are obtained.

후처리

  1. temperatureis maintained below −40° C
  2. stirringthe mixture is kept stirred while the temperature
  3. customto rise to 10° C
  4. washthe organic phase is washed with a saturated NaHCO3 solution, with water
  5. extractionextracted with ether
  6. dry with materialthe organic phase is dried over Na2SO4
  7. customthe solvent is evaporated under vacuum
  8. customthe crystallized product formed

출처 및 근거

ORD 기록
ord-dcee23b234cb471cbb314143425b6c0f
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07687537B2

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